GB969024A - Dihydrodibenzocycloheptene carboxylic acid esters - Google Patents
Dihydrodibenzocycloheptene carboxylic acid estersInfo
- Publication number
- GB969024A GB969024A GB15355/61A GB1535561A GB969024A GB 969024 A GB969024 A GB 969024A GB 15355/61 A GB15355/61 A GB 15355/61A GB 1535561 A GB1535561 A GB 1535561A GB 969024 A GB969024 A GB 969024A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- cycloheptene
- dibenzo
- dihydro
- reacting
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 Dihydrodibenzocycloheptene carboxylic acid esters Chemical class 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- VMEJOUNZMMHCLC-UHFFFAOYSA-N 6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulene-11-carboxylic acid Chemical compound C1CC2=CC=CC=C2C(C(=O)O)C2=CC=CC=C21 VMEJOUNZMMHCLC-UHFFFAOYSA-N 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- POAVRNPUPPJLKZ-UHFFFAOYSA-N 6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-ol Chemical compound C1CC2=CC=CC=C2C(O)C2=CC=CC=C21 POAVRNPUPPJLKZ-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 229910000799 K alloy Inorganic materials 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000001078 anti-cholinergic effect Effects 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000000812 cholinergic antagonist Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 150000003112 potassium compounds Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 230000002048 spasmolytic effect Effects 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention comprises esters of 10, 11-dihydro -5H- dibenzo (a, d) cycloheptene -5- carboxylic acid, of the general formula: <FORM:0969024/C1/1> (wherein R1 represents an alkyl or dialkylaminoalkyl group, a saturated mononuclear nitrogen-containing heterocyclic group attached to the oxygen atom through carbon and optionally carrying one or more alkyl groups, or a tropinyl or pseudotropinyl radical, the term "alkyl" denoting groups containing not more than 7 carbon atoms), and their non-toxic acid addition salts when R1 is a basic radical, and the preparation thereof by reacting under esterification conditions the parent acid or a reactive functional derivative thereof with an alcohol R1OH, or a salt of the acid with a reactive functional derivative of the alcohol. 10, 11-Dihydro -5H- dibenzo (a, d) cycloheptene -5- carboxylic acid is prepared by alkaline hydrolysis of its nitrile (followed by treatment of the resulting salt with an acid), or by converting 10, 11-dihydro -5H- dibenzo (a, d) cycloheptene -5- ol (see Specification 15354/61) into its methyl ether (e.g. by reaction with methanol in the presence of concentrated hydrochloric acid), reacting the ether with a sodium-potassium alloy to replace the methoxy group by potassium, and reacting the resulting potassium compound with carbon dioxide. The acid may be converted into its acid chloride by the action of thionyl chloride, and into its sodium salt by the action of sodium in toluene. Its nitrile is prepared by reacting a 5-halo-10, 11-dihydro -5H- dibenzo (a, d) cycloheptene (see Specification 969,023) with a metal cyanide, e.g. cuprous cyanide. Pharmaceutical preparations comprise the compounds of the invention in association with a pharmacologically acceptable carrier. They have anticholinergic, spasmolytic and analgesic activity, and may take the form of tablets, pills, capsules, suspensions, emulsions, syrups or elixirs.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15355/61A GB969024A (en) | 1961-04-27 | 1961-04-27 | Dihydrodibenzocycloheptene carboxylic acid esters |
| DK188362AA DK104843C (en) | 1961-04-27 | 1962-04-26 | Process for the preparation of esters 10,11-dihydro-5H-dibenzo (a, d) cyclohepten-5-carboxylic acid. |
| BR138472/62A BR6238472D0 (en) | 1961-04-27 | 1962-04-26 | PROCESS TO PREPARE 10,11-DI-HYDRO-DI-BENZO CYCLOPETHENE-5-CARBOXYLIC ACID AND ITS ESTERS |
| FR895817A FR1324513A (en) | 1961-04-27 | 1962-04-27 | Process for the preparation of dihydro-dibenzocyclo-heptene carboxylic acids and their esters |
| DEN21509A DE1242605B (en) | 1961-04-27 | 1962-04-27 | Process for the preparation of anticholinergic esters of dibenzo- [a, d] -cycloheptane-5-carboxylic acid |
| FR905129A FR1969M (en) | 1961-04-27 | 1962-07-26 | Dihydro-dibenzocyclo-heptene carboxylic acids and their esters. |
| US377520A US3264308A (en) | 1961-04-27 | 1964-06-24 | Dihydrodibenzocycloheptene carboxylic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15355/61A GB969024A (en) | 1961-04-27 | 1961-04-27 | Dihydrodibenzocycloheptene carboxylic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB969024A true GB969024A (en) | 1964-09-09 |
Family
ID=10057685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB15355/61A Expired GB969024A (en) | 1961-04-27 | 1961-04-27 | Dihydrodibenzocycloheptene carboxylic acid esters |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3264308A (en) |
| BR (1) | BR6238472D0 (en) |
| DE (1) | DE1242605B (en) |
| DK (1) | DK104843C (en) |
| FR (2) | FR1324513A (en) |
| GB (1) | GB969024A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1107036A (en) * | 1964-10-31 | 1968-03-20 | Koninklijke Pharma Fab Nv | Esters of dibenzocycloheptenyl-carboxylic acids |
| US3527763A (en) * | 1965-09-01 | 1970-09-08 | Koninklijke Pharma Fab Nv | 5-hydroxy-dibenzocyclohepten-5-yl-carboxylates |
| GB1273823A (en) * | 1968-10-22 | 1972-05-10 | Soc Ind Fab Antibiotiques Sifa | New tropane derivatives their salts and process for preparation thereof |
| US4182896A (en) * | 1974-02-07 | 1980-01-08 | Societe Hexachimie | Indane derivatives |
| DE3243981A1 (en) * | 1982-11-27 | 1984-05-30 | Rütgerswerke AG, 6000 Frankfurt | METHOD FOR THE PRODUCTION OF FLUOREN-9-CARBONIC ACID |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3049438A (en) * | 1957-11-26 | 1962-08-14 | American Cyanamid Co | Pyridotriazole brighteners |
| US3058989A (en) * | 1957-11-26 | 1962-10-16 | American Cyanamid Co | Pyridotriazole brighteners |
| US3222371A (en) * | 1962-04-19 | 1965-12-07 | American Cyanamid Co | Pyridotriazole brighteners |
-
1961
- 1961-04-27 GB GB15355/61A patent/GB969024A/en not_active Expired
-
1962
- 1962-04-26 BR BR138472/62A patent/BR6238472D0/en unknown
- 1962-04-26 DK DK188362AA patent/DK104843C/en active
- 1962-04-27 DE DEN21509A patent/DE1242605B/en active Pending
- 1962-04-27 FR FR895817A patent/FR1324513A/en not_active Expired
- 1962-07-26 FR FR905129A patent/FR1969M/en active Active
-
1964
- 1964-06-24 US US377520A patent/US3264308A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR1324513A (en) | 1963-04-19 |
| US3264308A (en) | 1966-08-02 |
| DK104843C (en) | 1966-07-11 |
| BR6238472D0 (en) | 1973-05-24 |
| FR1969M (en) | 1963-08-12 |
| DE1242605B (en) | 1967-06-22 |
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